Contestshipping Week 2016
by swimming-toon-lover
Summary: Pokeshipping week worked out so well, so I decided to give my other kids a shot this year too. Contestshipping week prompts.
1. Chapter 1

May and Drew make me ramble. Have some fluff I threw together because I'm a terrible procrastinator.

CS week 2016 Day 1- Alola

May was born for the beach.

Many things had changed in the five years since she'd left home, but her love of adventure was not one of them. She loved every new place, from the snowy peaks of Sinnoh to the sleepy country sides of Kanto she'd yet to find a place she couldn't find something to entrance her, but if she was being completely honest, beaches would always be her favorite type of place.

Alola was magic.

The cluster of islands was only just beginning to make a push to attract trainers of all types to its remote local, and May had jumped at the invitation to participate in a Contest showcase on the biggest of the tropical islands. The second the plane door was open she was off it, and sprinting off the simple airstrip straight to the beach it bordered. She spread her arms wide and closed her eyes, breathing in the ocean air she'd missed so much while she'd been making her way through the Sinnoh circuit the last year. She listened to the waves roll in and the odd bird type she couldn't identify cawing overhead.

"One of these days I'm going to let you lose all of your stuff."

May's gentle smile broke into a wide grin. She took one more moment to appreciate the breeze before turning around.

"But then what would be the point in keeping you around?"

Drew snorted and flicked his hair, two things that were so endearingly him that May could hardly believe that they'd once been almost guaranteed to send her into a rage. There were two bags at his feet, and May skipped toward him and picked up the yellow one.

"It's cool though, right, that the planes land right here on the beach? How cool is that?" She knew she was bouncing, but she didn't care. Drew only grinned at her.

"Pretty cool actually. Everything about this place is pretty cool." He picked up his own purple bag and motioned with his head toward the airport. "We need to go this way if we're actually going to get anywhere."

May smiled then started walking with him, falling easily into step on his left. He'd spent the entire plane ride answering her incessant questions about Alola, which she'd been shocked to learn he'd been to several times on vacations with his family. She maybe shouldn't have been, anymore it was safer to assume Drew _had_ been somewhere, but she still couldn't believe he'd never mentioned that he'd gone to the paradise region so regularly. She planned on talking about the place every day for the rest of her life and she'd only been in it for ten minutes.

"Are you going to play tour guide the whole time?" she asked as they reached a sleek but tough looking jeep on the other side of the airstrip. Drew simply smirked and pulled open the door to the back seat. May rolled her eyes at him before sliding in.

"Fine, have it your way, but be warned, I plan on spending at least one full day on the beach." Drew slid in next to her, and the door clicked shut behind him. She shot a sidelong glance at him, trying to read his expression, but quickly looked forward again as her stomach swooped. She still wasn't used to this. Drew had always made her feel things; anger, annoyance, confusion, frustration…

Well, that one was still there now.

But now it was different. It had been different ever since he'd said they should go to Alola together. It had been different since Harley and Solidad and Zoey and Dawn had all said they wouldn't be going. It had been different since this trip was intentionally only the two of them.

May could feel her face heating up, and fought the desire to scoot further into the backseat of the jeep away from the heaviness that was Drew. She chanced another glance only to see him looking at her from the corner of his own eye. He quirked an eyebrow and she huffed and laughed awkwardly, then yelped as the jeep lurched forward and she lost her balance and tumbled into him. Drew's arm went around her automatically to steady her, and though the driver told her to be careful back there, she barely noticed. Sparks were crackling along her arms, and she was staring, but he was too.

One breath. Two. Three.

"Seat belts."

May blinked, and shifted around to try and buckle the belt.

Drew didn't let go.

They both knew what this trip was. It wasn't as though they didn't know what was going on. They'd been doing this dance for months now, years really, but neither of them was going to actually admit that. It was so obvious that they were on the verge of something, but there was still doubt sitting at the back of May's brain.

What if she was reading more into it than he was?

What if he was fine with the way things were, all tense and awkward but also wonderful and working? What if acknowledging whatever was between them ruined it? What if it only worked if they stayed on the surface.

"Are you okay?"

He finally let go, but didn't move away. Their legs were touching, and that was the only part of May's body that had any sensation.

"Fine!" she squeaked. "Just excited for another expedition." She brought her hands up to frame his face and closed an eye, pretending to focus her shot.

"Adventures in Alola! Beaches, cliffs, waterfalls…as long as everyone remembers to stay away from edges it should be amazing!"

"Are you ever going to let that go?" Drew complained, frowning at her.

"Nope!" she said happily. Drew groaned.

May turned her attention out to the scenery rolling past them, keeping her hands up. Alola really was amazing. Everything was so green and there were so many bright colors, either flowers or the houses lining the road. They were driving toward a beach, but May sort of assumed that was a given. The place was small, made all the more obvious that it only took about three minutes for their car ride to come to an end.

"Whoa."

May had never really stayed anywhere that wasn't a Pokémon Center, but she hadn't been in charge of this trip. The contest people were putting them up, and apparently they were doing it style.

"This is actually one of the biggest resorts in the region. We never stayed here, we tended to go smaller, but this place still has an amazing reputation." Drew explained as he walked back up to her. He'd left her gaping around the lobby to go to the front desk "in the interest of actually getting to a room sometime in the next day," and was now holding an electronic keycard in front of her face to get her attention.

"Do you want to drop your stuff in your room?"

May focused on him then.

" _My_ room?"

May felt a little thrill at the soft pink that made its way across Drew's cheeks. She always felt so proud when she could make him blush.

"Well, yeah…why wouldn't you…oh right group travel."

May giggled.

"I guess I should get used to having my own room now that I'm a big shot, huh?"

"Yeah, the girl trespassing on the beach finally made it into the resort." Drew said.

"What's that supposed to mean?" May asked, frowning at Drew, who had started to walk the second he'd finished. She loped after him.

He seemed embarrassed, which normally would have been cause for amusement, but now she wasn't sure if she was supposed to be offended or not.

"You know…the beach is only for people staying in the resort?" He said.

"What are you talking about?"

May was beyond lost, and judging by Drew's reaction that was a bad thing.

"Nothing. Let's just head to the beach."

Drew was obviously done talking about whatever it was May wasn't getting, because he picked up his pace and it wasn't until he was at a pre-set umbrella and loungers that she caught up to him. He was in "off mode" now, and May wasn't sure how that had happened. Another wave of anxiety over the changing nature of their relationship washed over her. Was this how it was going to be? If they got more…serious…was Drew always going to be this, well, serious?

May was so distracted that she hadn't even noticed Drew had stripped off his outer layer of clothing and was now sitting in his lounger in swim trunks, eyes obscured by a very cool pair of black sunglasses. She gulped, but his agitation was still very evident in the way his eyebrows pulled under the glass frames, and how he was frowning at the beach, where the sun was already low. She shook herself and pulled off her own tank top and shorts to reveal the bright red bikini she and Dawn had spent two hours picking out in a video shopping trip that had proven very difficult.

She crawled onto the second lounger and perched her own white sunglasses on her nose. She glanced at Drew again, but he was still staring at the surf, so she turned to do the same.

"Do you really not remember?"

May shivered as Drew's voice broke the full minute of silent tension.

"Remember what?" She turned her head to him, but he was still looking away.

"Slateport?"

"What about Slateport?" May asked, the feeling that she was missing something important burning in her throat. He looked at her, indignation obvious even behind the sunglasses.

"That was when we met, May." He said.

"You mean when you made fun of me and bragged about staying in that fancy resort, and literally stuck your hand in my face?" She asked, trying not to laugh.

"Well, yeah, okay, when you say it like that it's not nearly as nostalgic as I was making it in my head."

May's heart skipped.

"You think about when we met as nostalgic?" She asked. He raised an eyebrow.

"How is the first time you meet someone not nostalgic?" May shrugged.

"Don't get me wrong, you made an impression," She grinned, retreating back into the safety of joking, "but it wasn't exactly a good one." Drew pushed his glasses up onto the top of his head, sweeping his hair back with them. May swallowed thickly, then felt her face flushing, hoping he hadn't noticed.

"Okay, so the first beach was a little…rough, but what about the other times?" He asked, and she couldn't tell from his tone if he was being serious. Frustration flared up in her again, but this time she only had herself to blame.

May pushed her own glasses up. The sun was nearly gone now, and the light was low. She glanced up to answer him, but Drew had moved, and was standing above her, holding out a hand. She took it, and he pulled her up, but he didn't let go when she expected him to. Instead he started walking toward the water, dragging her along with him.

"What other times?" she asked, because she had to say something before she exploded. Drew studied her.

"The same night, at Slateport." May frowned.

"But, you weren't there to watch the fireworks…were you?" He smiled.

"I suppose there were fireworks to watch too, weren't there."

May wasn't sure if her heart was still beating, or if it was just going fast enough to seem like it had.

"What other-"

"After the first Ribbon Cup."

"Ah yes, the first of many post cup training sessions." May grinned, but Drew's smile didn't hold amusement, it was sincere, and May had to look away again.

"What is your point here?"

"I think I really like the beach." May looked quickly up at him. He was still holding her hand, but he moved it slightly, and May realized it was her turn.

She could let go right there, and they'd go back to gliding along in silent but familiar agony, to never being sure if they were _serious_ or…

No.

She spread her fingers and slid them so that they interlocked with his.

"I love beaches." she whispered. "They're by far my favorite travel destination." She shifted, and realized for the first time that she had to tilt her gaze up to look at him.

When had that happened?

"May…"

He sighed, and May waited. Drew had to have a plan; he always had a plan. He had plans for when she didn't, and it was the only reason she had made it this far. She just had to wait now, for him to put it in action.

His free hand entered the pocket of his trunks, and when it came out, he was holding a bright red flower, which would have been entirely normal, only for once it wasn't a rose.

"I know this isn't my regular thing, but…"

He held up the Alolan flower between them, and May smiled at it before he reached up and pushed it behind her ear.

"Drew-"

May was glad when he shook his head, because she honestly had no idea what she was going to say. It was just like the jeep, but a million times worse.

No, _better_.

They were staring at each other. Drew's normally bright green eyes were a darker emerald in the low lighting and they were absolutely fascinating. Did they always do that? She'd have to remember to check. Maybe they were still bright, but she just needed to get closer…

She leaned up, and they weren't green anymore. They were black, because they were all pupil. May realized too late what she had done, but then again maybe she had meant to do it. Forget the status quo. May wasn't status quo, May was adventure, and adventure was going for this.

The hand Drew had used to put the flower behind her ear was still there, and she felt the gentle pull forward as he leaned down to match her. She had one last brief glimpse of what little green was left in his eyes before she closed her own. Every sensation she'd felt since the plane landed exploded in her at once. Her stomach swooped, her heart stopped and then raced ahead, and her face glowed with heat that radiated from where Drew's lips met hers.

May was born for the beach, and Alola was magic.


	2. Day 3 Meeting the Family

Well, I knew this one was going to get away from me, and it did. Into a multi-chapter fic did. So…here is an excerpt for this week, and then I will post the full version at the end.

Day 3- Meeting the Family

They were silent as he guided her through the vast hallways. May couldn't help but be amazed, despite everything running through her head at the seamless blend of the technology LaRousse was known for and the ancient flair the house had. Finally Drew threw open half of a set of double doors and slung her forward, probably a bit harder than he meant to, and slammed the door shut again with his body.

"What just happened?" May asked, worrying a little over how agitated Drew looked. "For about thirty seconds there I thought it was going great and you'd been exaggerating about how horrible they were, but then…"

Drew sighed, and moved past her into the room. May followed as he made his way to the massive canopy bed and flung himself face down onto it.

"That actually was pretty tame." he mumbled into the duvet. May huffed and shoved his shoulder so that he rolled over onto his back.

"Okay, first of all, no, it wasn't. And second, you're going to have to do better than that, because I'm not going back into a room with them until I get some background."

Drew took a dramatic breath, and rolled slightly to look up at her.

"My dad doesn't think that training Pokémon is a real job. Especially not Contests. Like he said, they put up with it when I was younger, encouraged it even. They figured it would teach me responsibility, being out on my own like that. They were trainers themselves, even, but they gave it up for the "adult life", and when I turned 18 they told me I had to do the same."

May skipped and bounced as she landed on the bed next to him, settling in by leaning back on her hands.

"I remember that…sort of. You mostly just got really moody that whole year. That was also the year you won your second ribbon cup." Drew raised his eyebrows knowingly.

"I always knew that deep down they saw what I was doing as a hobby. But I thought, maybe if I was good enough, they'd see that I was serious about it. That that's what I wanted to do with the rest of my life. I never had any interest in what my dad does."

"But your sister has?" May asked. Drew sighed.

"Katie lives for it. She's amazing with business and tech, she's already running almost everything. Dad doesn't even realize."

"But he still seems to think that you need to walk away from what you love and take what your sister loves away."

"Patriarchy dies hard." He said, flinging his arms up and letting them crash theatrically back down beside him, crashing into May's as he did. She sighed, slid down so that she was lying next to him, and laced their fingers together.

"Hey, at least they approve of me." She said with a weak smile. She turned her head to look at him, and he turned too so that their noses were centimeters apart.

"Of course they do. You're royalty." May laughed once, and Drew smiled.

"Right."

"I'm sort of serious." He said softly. "You are about the only part of my life they do approve of. Unfortunately it's because they see you as a trophy, but I suspect they'll approve a little less when I let you yell at them later."

"And what makes you think I want to yell at them?" May teased, bumping his arm.

"You won't take them wanting to shut me up in an office building laying down. You won't take well to being used as a pawn in their game either. Also, you sort of already did." May narrowed her eyes.

"What if I like the idea of being a kept woman, huh? What if this was my plan all along? Retire from all that grueling training into the life of a LaRousse socialite?"

"Not funny." Drew said, and May dropped her eyes.

"Sorry." Drew sighed.

"I know you're just trying to help. And I know that in their own way they really are just trying to look out for me. I just wish they could see how stupid it is. They're so worried about legacy, but Katie is right there chomping at the bit and they won't see it. I'm happy the way I am, and they won't see it."

"They see how happy you are." May corrected, and Drew cocked an eyebrow at her. She sat up, and he heaved himself along too.

"Really, they do. That's why they're pushing it so hard." she explained.

"How do you know?" he asked. May rolled her eyes.

"You heard them. They think you bringing me here means you're ready to settle down. That's probably why they thought it was a good idea to bring it up even though that is horrible first meeting conversation." She rolled her eyes, and Drew smirked.

"Why does everyone say that, 'settle down?' What is it about marriage that means you have to stop your life in its tracks and stay in one place." he said. May shrugged.

"I never understood that either." she said.

"I mean really, I'm going to marry you, doesn't mean we're going to stop travelling." He grinned, but May lost control of her face.

"What?" she squeaked. Drew looked at her like she was crazy for a moment before realization dawned on his face.

"Oh! Well, I mean…if you…I just…and we…that is…" he was stuck, that much was obvious, but while he was stuck with words on, May was stuck with them off. She blinked slowly, and images started flooding her mind's eye like a movie. A beautiful beach at sunset, flowers everywhere and herself and Drew under a cute archway. The two of them making their way around contests circuits, just as they always had, but with a new sense of connection, and new rings on their fingers. The two of them holding hands and watching as a group of little kids with green hair and blue eyes ran around playing with their pokémon.

"Drew." She finally said when she realized he was still spouting off random verbs. He stopped.

"Sorry." he said.

"No." she shook her head. "Don't be." She grinned. "We aren't going to stop traveling when we get married. Your parents are just going to have to suffer with the utter torture of your perfect, amazing sister being in charge, because we're going to be living our own, fabulous royal lives." Drew laughed.

"You're going to marry me? Even with my crazy parents?" She said, knocking her knee into his and grinning at him.

"Only if that's not actually your proposal." He leaned forward and pressed his lips to hers softly before resting their foreheads together. They stayed like that for a moment before he leaned forward again and tackled her into the unbelievably soft bedcovers. She giggled as he burrowed his nose into her neck and attempted to tickle her before wrapping his arms tightly around her and holding her so that they were nose to nose again. She looked at him through her lashes. He kissed her nose, then smiled at her.

"Deal."


	3. Children

As with Pokeshipping week, I had intended to do all new pieces for this week, but it just so happened that I have a one-shot that I wrote awhile back about May and Drew and their twin daughters getting ready to start their journey that I actually really love, so I'm going to use it!

Some background on my future HC's here to give this piece some context: May and Drew have three kids, identical twin girls named June and Juli (pronounced Julie) and a son, Braylen. Also, June's favorite color is pink, and she wears it almost exclusively. For Juli it's baby blue, and the color difference is how most people tell them apart.

"We have something for you!" May beamed, and June's face took on a mixture of confusion and delight that really only she could pull off. Juli shrank back a little farther, not wanting to be seen as her father moved around to her twin's other side. She knew she shouldn't be spying; their parents had asked to speak to June alone. That almost never happened. The two of them separate from Braylen sure, but try as she might Juli could not come up with a reason her parents would need to speak to _just_ June.

Then she remembered that they would be leaving home soon, and even though they were going together, they wouldn't be doing the same thing. June would start entering contests, following in their parent's footsteps with her dream of becoming a top coordinator. Juli would be challenging gyms, hoping to dethrone Uncle Ash as Pokémon Master. She'd never given it a second thought, that maybe her parents would have more interest when it came to June's journey. As soon as it occurred to her however, she could think of nothing else and had high tailed it back to eavesdrop.

Now she tried to reign in whatever it was that was bubbling up inside of her (jealousy? anger? sadness?) and not give herself away.

"We wanted you to have something very special to us." her dad said, reaching for something she couldn't see.

"Sort of like a good luck charm!" her mom added. Her dad shot her a look of mingled exasperation and adoration, the default look he had with her.

"Or inspiration, because-"

"Luck is just good preparation." June recited out loud as Juli mouthed along out of habit. Drew nodded, and May rolled her eyes.

"Anyway, we thought you'd like…" Their parents each held a hand out toward June, but Juli couldn't see what was in them. June filled in the blanks.

"Are these your ribbons?" she breathed, reaching out to touch their mother's.

"Our first ribbons." May clarified. Juli's eye's narrowed as June squeaked excitedly.

"That's so amazing!" June looked up at their smiling parents. "and one is pink and the other is blue; it's perfect!" Juli straightened, more curious now.

 _Blue and pink…just like.._

"We thought you'd like that." Drew said. "Here." They each stepped toward June, and they pinned the ribbons to the straps of her tank top. The pink one blended in, but the blue one stood out against the pale fabric.

"We're so excited for you." May said, standing back and admiring her handiwork. "You're going to have so much fun." June beamed at her.

"You're a natural, you'll have your own ribbons in no time." Drew put in, looking prouder than Juli could ever remember seeing him. She bit her lip, then scurried off back to their room. She didn't think she could watch anymore without giving herself away.

She hadn't thought her parents would show a bias like that. Of course she knew they were both top coordinators, and that they'd probably always have more insight into June's journey than hers, but she had been expecting equal _investment_ in her own. Their father talked to Sakura about her gym challenges almost every two weeks for goodness sake! Obviously she had been wrong. Obviously June following in their footsteps meant more to them.

She flopped down on her blue bedspread and glared over at the pink half of the room. How could she have been so _stupid_?

The door opened, but she didn't look up. She didn't want to take this out on her sister, after all this wasn't her fault, but if she looked at those ribbons she wouldn't be able to stop herself from snapping at her.

"Jules."

It wasn't her sister.

She sat up sharply, not bothering to hide her glare.

"Done with the heir to the contest throne?" she said airily. Her parents exchanged a look, then fixed their confused gazes on her.

"What is that supposed to mean?" her father asked gently. Juli glared at him some more, and didn't reply.

"Okay…" he said, looking imploringly toward May, who stepped forward.

"We just wanted to give you a going away present." she said.

"Oh?" Juli spat. "and what might that be? A new watch? Some Pokeblock…no, sorry, that's for _contests_." she huffed, ignoring the looks of comprehension that flashed on her parent's faces.

"I knew we should've given them their stuff together." Drew said. Juli glanced at him from between her green bangs.

"I thought it would mean more if we gave them theirs individually." May pouted. Juli felt guilt wash over her in spite of herself.

"Juli, you saw what we gave June, didn't you?" her father asked. Juli nodded.

"And I guess I should've known better than to think I could not do contests and still be just as important. But gyms weren't your history. Gyms aren't you, so-"

"Gyms are just as important." May interrupted. "I grew up in a gym after all." Juli frowned. She had chosen to ignore that detail in her rush to feel slighted. "And your uncle Max is a gym leader now too." Juli blinked.

"I-" she took a deep breath. "Still; it's not like you can give me-"

With his ever present flair for the dramatic, her father cut her off by holding out his hand, something small and silver resting on his palm.

"My first gym badge?" he said with a smirk. Juli's mouth opened and closed like a Magikarp out of water. Her mother giggled.

"But…you never…" she squinted at the badge, which was two circles connected by a thin bar. "That's a balance badge!" she exclaimed. Drew's smirk morphed into a smile, and May grinned.

"But that can't have been your first. You have to have four badges to be able to challenge the Petalburg Gym." Juli pointed out.

"Very astute." Drew commended. "I was a bit of a special case." he glanced toward his wife who was still smiling immensely.

"Your grandpa accepted his challenge without the other badges. He seemed to think he needed to prove that a coordinator could be just as tough as a gym leader." she sounded amused, and Juli couldn't help but grin at her parents.

"So you beat grandpa Norman in a gym battle?" she clarified. Drew nodded, and Juli reached forward and took the badge, studying it.

"You come from a long line of gym leaders." May said. "It's just as important as contests."

"You come from a long line of strong _trainers_ ," Drew pointed out, "who can do anything." Julie sniffed, and blinked rapidly, refusing to cry.

"So, you don't care more about June's contests?" she asked. Her mom surged forward and engulfed her in a smothering hug.

"Of course not!" she shouted. "All three of you are important, no matter what you do." Juli peaked up at her dad over her mom's shoulder. He nodded and smiled. Juli buried her head into May's hair.

"Oh, what did they give you?" June entered the room and strode over, plopping herself down next to her twin. Juli held out the badge as their mother released her.

"So cool!" June clapped her hands together, then threw her arms around her sister. "I'm so excited!" she yelled, laughing. Juli joined in.

"Me too." she returned the hug, noticing as she did the small flash of movement from the doorway. She frowned a little.

If her parents were giving them their firsts as good luck charms to start their journey…

What was going to be left for Braylen?

May and Drew sat in bed that night listening for the twins excited chatter to die down. May, for one, couldn't be prouder of herself. They had managed to come up with the most amazing good luck charms for the girls. But, as usual, Drew had to spoil her fun.

"You know we just painted ourselves into a corner, right?" he said, glancing at her.

"What?" she asked, putting on her best confused face.

"May, I know you saw him too." Drew observed. She bit her lip, but Drew continued. "Don't try and pretend, I'm serious. How did we not consider that?" May frowned.

"We've still got at least three years to think of something." she ventured. Drew scoffed.

"Three years doesn't make new firsts appear May. We both know he's going to want to battle too, and the badge thing was already a stretch with Juli." May scrunched her face up in concentration.

"Maybe we can…um…we could…" she had nothing, and Drew knew it. "Why is this so hard?" she pouted.

"Hey, you're-"

"Nu uh!" she cut him off. Joking or not, she hated when Drew pointed out that he'd only ever wanted one kid in the first place. He frowned, but his face did hold a hint of an apology, so she let it go.

"Okay, but the point stands. We don't have anything left for Braylen." he said.

"Juli was really upset." May changed the subject, though admittedly probably not in the right direction. She didn't want to dwell on Braylen anymore, and she was actually really worried about what Juli had said. Drew only shrugged.

"We should've done them together." May added.

"That would've only made it worse." Drew said. May looked at him quizzically. "She wasn't upset because we did them separately. She was upset because she thought our first ribbons were more meaningful."

"To our careers maybe, but that badge means way more to _us_." May said. Drew raised an eyebrow at her.

"How is a ten year old supposed to realize that on her own? Someday she'll understand, but today she was just a kid who saw her parents giving her sister something with much more obvious emotional value." May huffed.

"I thought we made it perfectly clear that we are just as supportive of her gym battles. It doesn't matter if she doesn't want anything to do with Pokémon." Drew rolled his eyes.

"May, you lied to your parents about your journey to keep them happy for how long?" she smiled sheepishly. "Exactly." he added. "We just have to give her more time, and make sure we show just as obvious of an interest in her progress as June's, give her just as much help and advice." May looked up.

"Are you sure she's going to be alright?" a loud peal of laughter echoed through the walls, and Drew smiled at the sound of his daughters.

"I think she'll be fine. They've got each other after all."


End file.
